Wilhelm hebzbebg-



UNITED STATES PATENT OFFICE.

WILHELM HERZLBERG, OF BERLIN-WILMERSDORF, AND OSWALD SCHARFENBERG, OF BERLIN-SGHONEBERG, GERMANY, ASSIGNORS TO ACTIEN GESELDSCHAFT FUR ANILIN FABRIKATION, OF BERLIN, GERMANY.

ORTHOOXYAZO DYES.

No Drawing.

To idiom it may concern:

Be known that we, VlLI-IELM Hnnzenno and Usunzln flonnnrnnnnao, citizens of the German Republic, residing at Berlin-u ilinersdorl, Germany, and Berlin-Schoneberg, Germany, our P. 0. address being Prinzregentenstr. 10, l3crlin-lVilmersdorf, Germany, and liosenheimerstr. 12, Berlin Schoneberg, Germany, have invented certain new and useful Improvements in Orthooxyazo Dyes, of which the following is a specification.

By our invention by combining a di azotizcd 2-aminophenol derivative which contains negative radicals such as halogen with S-halogen-l-oxynaphthalene-5-sulf011ic acid new valuable dyestuffs for W001 are produced the chromium lakes having a very good fastness.

They form in the dry pulverized shape dart: powders soluble in water to a blue solution and are insoluble in alcohol, ether, 3611- zene, being destroyed by strong reducing .gents and dyeing on wool with aid of c iromium mordants blue tints.

The EZ-aminophenol derivatives containing negative radicals such as halogen which may be employed are represented by the general formula in which X stands for univalent substituents such as hydrogen, alkyl or halogen and at least one of these substituents is a negative group such as halogen.

The following examples illustrate our invention, the parts being by wei ht:

1. 17.8 parts of 2amino-4.6 dichlorophenol are diazotized by means of 6.9 parts of sodium nitrite and 50 parts of hydrochloric acid of 12 B. specific gravity. The diazo compound is allowed to run into a solution of 25.9 parts of 8-chloro-1-oxynaphthalene- 5-sulfonic acid, alkaline with sodium carbonate. The dyestuff is salted out and worked Application filed. August 30, 1921.

up as usual.

Specification of Letters Patent. Patented June 13, 1922.

Serial No. 496,971.

It dyes wool with chromium mordants blue tints of a very good fastness.

2. The diazo compound of 2i parts of 3.4.6-trichloro-2-aminophenol is coupled with 2.6 parts of S-chloro-loXynaphthalcne-5- sulfonic acid in a solution containing sodium carbonate. The dyestuff dyes wool with chromium inordants blue.

It is obvious that our invention not limited to the foregoing examples or to the details given therein. Similar dyes are obtained by substitution for the parent material in the foregoing examples other compounds within the foregoing definition.

W hat we claim is l. The herein described new ortho-oxy-azo dyes being in the shape of alkali metal salts, dark powders soluble in water to blue solution from which an inorganic or organic acid separates a red precipitation, the aqueous blue solutions becoming violet by addition of sodium carbonate, red by addition of sodium hydroxide, yielding upon reduction 8-chloro-2-amino-l-naphthol-S-sulfonic acid and a Q-aminophenol derivative, dyeing on wool with chromium inordants blue tints of a very good fastness and corresponding as free aclds to the general formula:

X meaning univalent substituents such as hydrogen, alkyl, halogen, at least one of these substituents being a negative group such as halogen.

2. The herein described new ortho-oxy-azo dyes being in the shape of alkali metal salts dark powders soluble in water to blue solutions from which an inorganic or organic acid separates a red precipitation, the aqueous blue solution becoming violet by addition or sodium carbonate, red by addition of sodium hydroxide, yielding upon reduction S-chloro-2-amino-1-oxynaphthalene-5-sulfonic acid and a halogenated 2- amino-l-oxy-benzene derivative, dyeing on wool with chromium mordants blue tints of a very good fastness and corresponding as free acids to the general formula:

qn (In; 0 1

X meaning univalent substituents such as hydrogen, alkyl, halogen, Y meaning halo gen. 3. The herein described ortho-oXy-azo dyes being in the shape of alkali metal salts dark powders soluble in water to blue solutions from which an inorganic or organic acid separates a red precipitation, the aqueous blue solution becoming violet by addition of sodium carbonate, red by addition of sodium hydroxide, yielding upon reduction 8-chloro- 2 amino-1-oxynaphthalene 5 sulfonic acid and a 6-dichloro-2amino-l-oxybenzene derivative, dyeing on wool with chromium mordants blue tints of a very good fastness and corresponding as free acids to the general formula:

X meaning univalent substituents such as hydrogen, alkyl, halogen.

4. The herein described new ortho-oxy-azo dyes being in the shape of alkali metal salts dark powders soluble in water to blue solutions from which an inorganic or organic acid separates a red precipitation, the aqueous blue solution becoming Violet by ad dition of sodium carbonate, red by addition of sodium hydroxide, yielding upon reduc- 'tion 8-chloro-2-amino-1-oxynaphthalene-5- sulfonic acid and a 4.6-dichloro-2-amino-1- oXy-benzene derivative, dyeing on wool with chromium mordants blue tints of a Very good fastness and corresponding as free acids to the formula:

o1 soni X meaning a univalent substituent such as hydrogen, alkyl, halogen.

5. The herein described ortho-oXy-azddye In testimony whereof we ailiX our signatures in presence of two witnesses.

WILHELM HEBZBERG. OSWALD SOHARFENBER-G.

Witnesses l GERHARD Horrn, RUDoLr HANGOVITZ. 

